Synthesis of amphiphilic poly(para‐phenylene)s by Suzuki polycondensation

1,4‐Dibromobenzenes carrying nonpolar hexoxy and polar oligo(ethylene glycol) side chains were subjected to Suzuki polycondensation with a benzene‐1,4‐bisboronic acid ester to produce high‐molar‐mass poly(para‐phenylene)s. The molar masses were determined with size exclusion chromatography with conventional polystyrene and universal calibration. These novel amphiphilically equipped rigid‐rod polymers have the potential to segregate lengthwise into polar and nonpolar domains, a property that has only rarely been described, and promise to exhibit novel interesting supramolecular properties. The oligo(ethylene gylcol) side chains terminate with a silyl‐protected alcohol group, and its deprotection on the polymer was proven to proceed quantitatively. This not only led to a further polarity increase but allows us to attach even more polar (e.g., charged) units in future projects. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 41: 2879–2889, 2003